DA-8159
乌地那非 西地那非磺酰胺 Chemical Name: 3-(1-Methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzenesulfonamide
CAS No. 268203-93-6, 319491-68-4
项目整合开发状态: Phase I
项目研究机构: Dong-A (Originator)
合成路线:The reaction of 5-(chlorosulfonyl)-2-propoxybenzoic acid (I) with 2-(1-methylpyrrolidin-2-yl)ethylamine (II) in acetone gives the sulfonamide (III),which is treated with 2,4,6-trichlorobenzozyl chloride (IV) and TEA to afford the active mixed anhydride (V).The condensation of (V) with 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (VI) in dichloromethane provides the corresponding carboxamide (VII).Finally,this compound is cyclized by means of tBu-OK in refluxing tert-butanol to furnish the target pyrrolo-pyrimidinone.
📌 参考资料/链接：
参考文献标题:Pyrazolopyrimidinone derivs.for the treatment of impotence
文献作者:Kim,S.; Kim,H.; Kim,D.S.; Chang,M.S.; Yoo,M.; Lim,J.I.; Ahn,B.O.; Kim,W.; Kim,I.Y.; Lim,T.K.; Kang,K.K.; Son,M.; Doh,M.; Shim,H.; Oh,T.; Kim,D.G.(Dong-A Pharmaceutical Co.,Ltd.)
参考来源:EP 1129093; WO 0027848
📄 详细内容
合成路线:The reaction of 2-propoxybenzoic acid (I) with SOCl2 in refluxing dichloromethane gives the acyl chloride (II),which is condensed with 4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide (III) by means of TEA and DMAP in dichloromethane to yield the carboxamide (IV).The sulfonation of (IV) with chlorosulfonic acid affords the benzenesulfonyl chloride (V),which is treated with 2-(1-methylpyrrolidin-2-yl)ethylamine (VI) in dichloromethane to afford the sulfonamide (VII).Finally,this compound is cyclized by means of tBu-OK in refluxing tert-butanol to provide the target pyrazolo-pyrimidininone.
参考文献标题:A process for preparing pyrazolopyrimidinone derivs.for the treatment of impotence
文献作者:Kim,S.-H.; Chang,M.-S.; Kim,D.-S.; Yoo,M.-H.; Kim,W.-B.; Bae,C.-J.; Kim,Y.-D.; Kim,E.-H.(Dong-A Pharmaceutical Co.,Ltd.)
参考来源:WO 0198304
产品链接: CAS No. 268203-93-6›› 产品链接: CAS No.319491-68-4››